


The trouble with love is

by Elerina_Tindomerel



Category: Gilmore Girls, Original Work
Genre: English Literature, F/M, Heartbreak, Loneliness, Lovesickness, Multiple Songs Songfic, Professor/Student Relationship, Romance, Slow Burn, Stanford University
Language: English
Status: In-Progress
Published: 2018-11-25
Updated: 2018-12-29
Packaged: 2019-08-26 02:20:17
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 3,189
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16672909
Author URL: https://archiveofourown.org/users/Elerina_Tindomerel/pseuds/Elerina_Tindomerel
Summary: Max Medina hasn't seen Lorelai for about a year, but he still can't forget her. It's seems impossible that another woman like her exists, so beautiful, enchanting, and altogether perfect. Max is about to give himself up completely, as he meets somebody new and starts to hope again. But things are much more complicated than anticipated. Will Max finally find his luck nevertheless?





	1. Prologue - The trouble with love

**Author's Note:**

> Hi everyone!
> 
> I recently looked for a Max Medina/reader fanfiction and found out there there aren't any, so I guess it's up to me to change that! :)
> 
> I really like Max as well as Scott Cohen (the actor) and it's quite a pity that he didn't return in "A year in the life". In my opinion, Max deserves that his story goes on, but as Lorelai is obviously made for Luke only, he has to find happiness somewhere else... Let's see if things will finally work out for him!
> 
> I hope that some of you love Max as much as I do and will enjoy this story! 
> 
> Elerína x
> 
> PS: English isn't my mother tongue, corrections in the comments as well as feedback and kudos are truly appreciated.

**Notes for the Chapter:**

> This is the prologue, the actual story begins in the next chapter. 
> 
> Feel free to listen to the mentioned songs, I'll include some of my favourites. But for the story it's sufficient to read the lyrics. :)

_Love can be a many splendored thing_  
_Can't deny the joy it brings_  
_A dozen roses, diamond rings_  
_Dreams for sale and fairy tales_  
_It'll make you hear a symphony_  
_And you just want the world to see_  
_But like a drug that makes you blind_  
_It'll fool ya every time_

_The trouble with love is_  
_It can tear you up inside_  
_Make your heart believe a lie_  
_It's stronger than your pride_  
_The trouble with love is_  
_It doesn't care how fast you fall_  
_And you can't refuse the call_  
_See you've got no say at all_

_Now I was once a fool it's true_  
_I played the game by all the rules_  
_But now my world's a deeper blue_  
_I'm sadder but I'm wiser too_  
_I swore I'd never love again_  
_I swore my heart would never mend_  
_Said love wasn't worth the pain_  
_But then I hear it call my name_

_The trouble with love is_  
_It can tear you up inside_  
_Make your heart believe a lie_  
_It's stronger than your pride_  
_The trouble with love is_  
_It doesn't care how fast you fall_  
_And you can't refuse the call_  
_See you've got no say at all_

_Every time I turn around_  
_I think I've got it all figured out_  
_My heart keeps callin'_  
_And I keep on fallin'_  
_Over and over again_  
_The sad story always ends the same_  
_Me standin' in the pourin' rain_  
_It seems no matter what I do_  
_It tears my heart in two_

_The trouble with love is_  
_It can tear you up inside_  
_Make your heart believe a lie_  
_It's stronger than your pride_  
_The trouble with love is_  
_It doesn't care how fast you fall_  
_And you can't refuse the call_  
_See you've got no say at all_

_(The trouble with love is ~ Kelly Clarkson)_


	2. I - When I was your man

**Summary for the Chapter:**

> Max spends his evening in a diner and makes a new acquaintance.

**Notes for the Chapter:**

> This first chapter took me a really long time to write, but I'm quite happy with the result. I also decided to add a gif at the beginning of every chapter. Enjoy! :)

Max Medina slowly stirred his cold coffee while listening to the soft music on the radio. He sighed. The summer break was over, the new semester at Stanford University would start tomorrow. His first class, English literature, was at eight a.m., and he definitely wasn't ready. At Chilton, he had been known as the pupils' favourite teacher, always happy; demanding but friendly. Max knew for sure that none of the students he taught last term would share this opinion. He was tired, exhausted and heartbroken. That sounded extremely clichéd, but it was true. Max just had the feeling to have no purpose, nothing to live for. Things with Diane hadn't worked out, he had known that right as they started dating because, well, he loved only _her_. He loved Lorelai Gilmore, more than anything. She had been the one woman he wanted to marry. Such a perfect person, beautiful, witty and admirable. He would have given her everything, he would have been a father for Rory and spent his whole life with them. But it wasn't meant to be. Lorelai didn't really love him, and he knew that it would have been a mistake to restart their relationship. She never would have been truly happy with him, but with every day without Lorelai Max realized how much _he_ needed her to be happy. He knew he shouldn't give up, that he grieved to long and let himself go. But up to now he just hadn't been able to regain hold. His job at Stanford had been the only thing to keep him alive, but teaching was no more a pleasure for Max. Everything was exhausting and difficult.

Max sighed again. The diner he sat in was almost empty now, he had to leave soon to prepare something for tomorrow and get some sleep. The first chords of the next song on the radio reached his ears, and Max immediately recognized the tune.

_Same bed but it feels just a little bit bigger now_  
_Our song on the radio but it don't sound the same_  
_When our friends talk about you, all it does is just tear me down_  
_'Cause my heart breaks a little when I hear your name_

_It all just sounds like ooh, ooh ooh ooh ooh_  
_Mm, too young, too dumb to realize_  
_That I should have bought you flowers_  
_And held your hand_  
_Should have gave you all my hours_  
_When I had the chance_  
_Take you to every party 'cause all you wanted to do was dance_

_Now my baby's dancing_  
_But she's dancing with another man_

_My pride, my ego, my needs, and my selfish ways_  
_Caused a good strong woman like you to walk out my life_  
_Now I never, never get to clean up the mess I made, oh_  
_And it haunts me every time I close my eyes_

_It all just sounds like ooh, ooh ooh ooh ooh_  
_Mm, too young, too dumb to realize_  
_That I should have bought you flowers_  
_And held your hand_  
_Should have gave you all my hours_  
_When I had the chance_  
_Take you to every party 'cause all you wanted to do was dance_

_Now my baby's dancing_  
_But she's dancing with another man_

_Although it hurts_  
_I'll be the first to say that I was wrong_  
_Oh, I know I'm probably much too late_  
_To try and apologize for my mistakes_  
_But I just want you to know_

_I hope he buys you flowers_  
_I hope he holds your hand_  
_Give you all his hours_  
_When he has the chance_  
_Take you to every party_  
_'Cause I remember how much you loved to dance_  
_Do all the things I should have done_  
_When I was your man_  
_Do all the things I should have done_  
_When I was your man_

_(When I was your man ~ Bruno Mars)_

He had always liked that one, but at this point it caused him to sadden even more. The guy in the song hadn't treated his girlfriend well or given her the attention she deserved. And now that she had left, he regretted what he did or did _not_ do. It was his fault that he was alone now, and he knew it. But Max hadn't made all these mistakes. He had spent all his time with Lorelai, he had held her hand and bought her a thousand yellow daisies. Still it hadn't worked out, even though he had done his best. And Max despaired so much because he couldn't blame himself, he couldn't apologize and try to put things straight. It was over, and it was nobody's fault. It was just over and he couldn't accept it. He missed her so much. 

"That's a beautiful song, isn't it?", a female voice asked. Max looked up slowly and saw that the person who had spoken was actually looking at _him_. It was a young woman with red hair and freckles all over her face. She was sitting a few stools away at the bar and in front of her on the counter lay a notepad and a few pencils. Her smile was warm and her voice was friendly, and even though she had surprised him, Max was glad about the diversion.

"It is indeed", Max answered and smiled as well, if only faintly. He looked at her more closely and decided that she somehow had a creative flair, as she wasn't dressed up but wore dungarees and had her hair pinned in an untidy bun. Max' impression was intensified by the fact that she was sitting alone in a diner with pen and paper at this time of the day. He vaguely pointed at the woman's supplies and asked: "Are you… writing?"

She looked down and blushed. Max watched her, intrigued by her manner. "No, I…", she began hesitatingly, "I'm drawing, actually." She looked up again, her cheeks still rosy.

"Oh", Max answered, surprised but interested. He thought about what else to say when the woman picked up the piece of paper in front of her and walked over to hand him the sheet. She then sat down on the nearest barstool, awaiting his reaction.

Max looked at the drawing in his hands and even though he was no art expert, he realized right away that it was a really good one. It was a monochrome picture, the woman had used only one pencil on the white paper, probably something like charcoal. The image motif seemed to be a man sitting somewhere and looking down at a cup in his hands, it was a side view and you could only see the man's upper body and his face profile. The whole drawing had a somewhat dramatic effect, because it was no detailed sketch, but the strokes were chaotic and you could only see the shown person if there was some distance between the viewer and the drawing. Still, some of the man's features were clearly recognizable and oddly familiar…

"That's me", Max stated matter-of-factly. The woman didn't say anything, but her silence told him that he was right. After this sudden realization, Max looked at the drawing in a different light. The man, he himself, seemed extremely outworn and looked, to put it mildly, absolutely awful.

Max glanced back at the artist. "Do I really look that terrible?", he asked her, and his question sounded much more distressed than he had intended.

The woman smiled, sympathetically. "You look quite tired. But I definitely exaggerated." She paused for a moment. "Do you… like it? I mean, despite… you know." The look on her face suggested that she was genuinely interested in Max' opinion.

"Yeah, it's great!", he answered truthfully, but added: "As far as I can judge, at least." Max smiled.

The woman looked at her drawing and then back at the man next to her. "Everybody can judge art in my opinion. And every judgement is correct as we all see something different while looking at the same picture."

Max smiled wider. He liked her way of talking. "Are you a professional artist?", he suggested and was slightly confused when she began to chuckle.

"Oh no", she answered, still grinning, "I just sell my drawings to earn some extra money. It's great to get paid for something you love to do, but I'm always sad about giving away my artworks."

"That makes perfect sense", Max answered. "But, if you don't mind my asking, what's your actual job, then?" He would have assumed that she was an author, but writing _and_ drawing seemed a bit too much to him.

"I'm going to be an English teacher soon", the woman said, and her smile made obvious that she was really passionate about it. "I love the English language and I simply adore British and American literature."

Max was pleasantly surprised. "I'm teaching English as well! With a focus on literature, in fact."

His interlocutress appeared to be very excited about this. "Wow, that's awesome! You need to tell me everything about your job! I love talking to kindred spirits."

Her enthusiasm took Max by surprise, and her childlike excitement painfully reminded him of Rory for a second. She had also always been so zealous and inquisitive. He missed her. She had been the paragon of a perfect daughter for him.

"Is everything alright?", the woman asked, sounding worried, "I really don't want to annoy you, I can leave now…"

"No! No, it's alright", Max interrupted her. "I just thought of a former student of mine." He looked up and tried to regain his smile. He really didn't want this conversation to end, he hadn't thought about Lorelai for the last 15 minutes and that was definitely a record. "I… I enjoy talking to kindred spirits as well. But let's start with you. Who's your favourite author, to begin with?" Max was not in the mood to talk about himself, but he was eager to learn something about her.

The woman grinned. "Have a guess!", she prompted, and Max was glad about her trying to bring back their earlier lightheartedness.

"Um…", Max reflected for some seconds, "Jane Austen would be fitting, but it's too clichéd for you I assume…"

"Wow, that's a really good guess!", the woman said truly amazed. "Correct country, almost the correct time, … I seem to be like an open book to you."

Max smiled about her reaction. "Okay, maybe… one of the Brontë sisters? Or George Eliot?"

"The time is also correct now, but you still have to find the right name." One could tell that they both had a lot of fun with this small game, much more fun than Max had had in ages.

"Oh, I think I know it!", Max exclaimed, "it's Thomas Hardy!"

"No, not really", she said, "you were quite right with the gender before. Besides, I always felt that his stories are a bit too excessive."

Max chuckled slightly because he absolutely shared her opinion. "Um… so it's neither Charles Dickens nor William Thackeray…", he pondered. "To be honest, I'm really running out of ideas."

"Well", the woman answered and smiled amusedly, probably because of Max' somewhat helpless expression, "I'll tell you the name of the protagonist of my favourite book, but this is the only hint you'll get." 

"Alright." Max straightened himself, being quite tense because his reputation as an English teacher was at hazard.

She smirked at him coquettishly and slowly said: "Margaret Hale."

Max was quite relieved but tried not to show it. "The book is 'North and South' then, so I conclude that your favourite author is Elizabeth Gaskell."

"Correct!" The woman smiled broadly. "What do you think?"

He looked at her for a second before he understood her question. "Oh, about your choice? It's a quite good one, I think. Gaskell came to a fine compromise between Austen's rather idyllic and Dickens' very negative depiction of their time. I prefer Charlotte Brontë, however."

His interlocutress nodded. "That's exactly the reason why I like her. But I also really enjoyed reading 'The Professor'."

"'The Professor'?", Max exclaimed, astonished. This novel by Charlotte Brontë was neither very known nor greatly admired, and it surprised him that she mentioned it. "So, affairs between teachers and their students entertain you?", he asked jokingly, perking his eyebrows up.

"No!", she answered and blushed again, raising her hands as if she wanted to push away the reproach, "I mean, that's not the point at least. It was interesting to learn what being a teacher meant back then, and in general I always read the rather unpopular books of an author as well to understand them better."

Max couldn't suppress a smile, because he seemed to have really hit the mark with his assumption. But what the woman next to him said thereafter impressed him. "That's a really good technique. I'm sure that you are an excellent teacher."

"I hope so", she answered, seeming quite flustered, "thank you."

He just opened his mouth to reply as the barista walked up to them behind the counter. "I'm sorry", he said, cleaning rag in hand, "but you have to leave now, we're closing."

Max looked at his watch and gasped slightly. Time had really flown by and he hadn't even noticed that the diner was completely empty except for the two of them.

"Of course!", he answered apologetically and stood up. While the woman gathered up her art supplies, he paid the bill for both of them. She thanked him, smiling coyly.

"Don't forget your drawing!", he exclaimed, as he saw that it still lay on the counter.

She looked at him and then at her artwork. "Oh… right", the woman muttered and hesitantly picked it up.

They left the diner alongside one another and in silence, not knowing what to say. As they stepped out, the cold air hit them. It was a cloudless, moonlit night that announced the approaching autumn. The woman shivered and crossed her arms. They stopped walking and turned towards each other in the middle of the almost empty parking lot.

"I hope…", Max began after they had both been silent for a while.

"You know…", the woman said in the same second, and they both stopped to let the other speak. Max made an inviting gesture, indicating that it was her turn to talk.

She smiled and repeated: "You know, I think you should keep this." She held the drawing out to him. 

"Are you sure?", Max answered sceptically, "you could still sell it or something."

"No, I want you to take it", the women said resolutely and gave him the piece of paper. "I don't think anyone would buy this anyway, it looks far too sorrowful", she added with a smirk.

Max smiled as well, looking down and then up again.

"What's your name by the way?", she asked.

"It's Max", he said, still smiling, "and yours?"

"I'm Samantha, but people call me Sam", she answered with the same facial expression.

"Alright, Sam. I… hope we'll see each other again", Max said, and he truly meant it.

Sam looked at him kindly. "I hope so, too, Max."

They said goodbye to each other, and as Max walked up to his car through the fresh nocturnal air, his thoughts only revolved around the red-haired woman. This had been the most comfortable and pleasant hour of his whole _year_. Samantha seemed to be an incredibly interesting person, and her whole behaviour and character differed so much from Lorelai's that she didn't remind him of her at all, but had managed to distract him from his feelings for an extraordinary long time. Max opened the car door and sighed. This couldn't be true, this couldn't actually be happening. It just seemed to easy. There had to be a catch. "Of course, you idiot", he thought to himself, "there is a catch, because you probably won't see her ever again. You didn't even ask for her number!" Max slumped in the driver's seat and leaned back, closing his eyes and sighing again. This had just been so unexpected, he hadn't had any time to think about it, and now it was too late. Besides, Max knew that he would be a fool all the more if he thought that he was now over Lorelai just like that. It was highly probable that tomorrow, everything would be how it had been when he had entered the diner.

Max opened his eyes again and looked at the drawing in his hands. He really looked awful, but Sam had somehow managed to make him look beautiful as well. She was really talented. For some reason, Max couldn't tell whether it was instinct or coincidence, he turned the piece of paper around, only to discover that Sam had scribbled her number on the back side. He smiled. Maybe this would actually work out. There didn't have to be a catch.

When Max arrived at his apartment, it was already very late, but he still managed to prepare something for his classes on the next day. He didn't feel extremely happy, but he also wasn't sad or exhausted. Through this encounter he had found a state of inner calmness that was incredibly soothing. That night, Max slept soundly for the first time in what felt like ages.

**Notes for the Chapter:**

> Feel free to leave kudos and comments! :)
> 
> Edit: If you'd like to read more, please leave a short comment! I'd love to continue this story if people are interested! 18th July 2019, Elerína x


End file.
